title: Palladium-catalyzed through-space C(sp(3))-H and C(sp(2))-H bond activation by 1,4-palladium migration: efficient synthesis of [3,4]-fused oxindoles.
abstract: Palladium two step: Linear anilides were converted into the title compounds in good to excellent yields through a palladium-catalyzed domino carbopalladation/1,4-palladium shift sequence. The C(sp(3) )-H activation involves a seven-membered palladacycle, and is chemoselective in the presence of competitive C(sp(2) )H bonds. DMA=N,N-dimethylacetamide, OPiv=pivalate.
authors.affiliation: Laboratory of Synthesis and Natural Products, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch.
authors.forename: Tiffany
authors.initials: T
authors.lastname: Piou
authors.forename: Ala
authors.initials: A
authors.lastname: Bunescu
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Luc
authors.initials: L
authors.lastname: Neuville
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000081:Acetamides / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*; D011789:Quantum Theory
chemical_list: D000081:Acetamides; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D010165:Palladium; D002244:Carbon; D006859:Hydrogen; C013959:dimethylacetamide
keywords: CH activation; chemoselectivity; heterocycles; palladium; synthetic methods